Hydrochloric Acid → HCID 178429523, compound

HRID 630243Notes

Reaction equation

HRID 630243 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:5]=[C:4]([OH:16])[CH:3]=1.[ClH:17].O1CCOCC1>CO>[ClH:17].[ClH:17].[CH3:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[N:11]=[CH:12][CH:13]=[CH:14][N:15]=2)[N:5]=[C:4]([OH:16])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178429522HCID 178429522, compound

Product 1

HCID 178429523HCID 178429523, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-methyl-2-[(pyrimidin-2-ylmethyl)sulfanyl]pyrimidin-4-ol (100 mg, 427 μmol) was stirred in methanol (10 mL), and a solution of 4 N HCl in dioxane (320 μL, 1.28 mmol) was added dropwise at 0° C. The mixture was stirred for 20 minutes at room temperature. The solvent was removed by evaporation, and the residue was triturated with diethyl ether, filtered, washed with ether, and dried in vacuo to afford 6-methyl-2-[(pyrimidin-2-ylmethyl)sulfanyl]pyrimidin-4-ol dihydrochloride (105 mg, 80% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.15 (s, 3H), 4.68 (s, 2H), 6.05 (bs, 1H), 7.44 (t, J=4.9 Hz, 1H), 8.79 (d, J=4.9 Hz, 2H); LRMS (ES4) m/z 235 (100%, M+1).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was triturated with diethyl ether
  3. filtrationfiltered
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c453bfb61f5b463589d428bab1a41a80
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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